Thank you all that helped me figure this issue out with their suggestions. I have, after some headaches, gotten this to work. As I has suspected it had to do with the TLS handshake with Gmail. I used Google to find quite a few instances of people doing close to the same thing. Overall what i did was this;

Make myself a CA
Make a Cert and sign it as the CA
Within Postfix:
Create a generic file with my local aliases and deliverable addressees Cretae a transport file with my domain and gmail's smtp port (I was getting this wrong in my first installation) Create the sasl_passwd file with my Gmail (Google Apps) email address and password.
  Hash the files (I forgot to hash one once in my troubleshooting)

After I had done that I could actually tail the logs and see the handshake occurring. So it is fixed and I am receiving mail! The interesting thing is that it appears (obviously I could be wrong) that Gmail requires a TLS connection for mail that is relayed. So just adding a ~/.forward or an alias was not working.

If anyone is interested I will be writing up a small tutorial on what I did in order to get it working and it will be posted some time this week. You will be able to read it here (http://www.planetmayfield.com/linux-unix/using-postfix-to-relay-local-mail-to-google-apps/ ).

Again thanks for all the suggestions.

---
Chad R Mayfield
[EMAIL PROTECTED]
GPG Key: 0C9A026F
http://www.planetmayfield.com/
http://www.chadmayfield.com/






On Feb 16, 2008, at 2:37 PM, [EMAIL PROTECTED] wrote:

Greetings All,

So I have been on SLLUG, PLUG, and the Ubuntu Utah lists for quite awhile under different addresses, but have not posted a questions yet, some responses, but no questions. I have enjoyed learning with everyone's posts but finally find myself needing help that I cannot resolve with Google's help alone, hopefully someone here can help.

On the main domain I host I use Google Apps for email only rather than have to administer a mail server a deal with spam issues, relays, etc.. The problem I am running into is that I need the local mail generated by localhost to be relayed/forwarded to my Google Apps account. My MX records are pointed toward Google's mail servers, while my domains A record is are pointed to the physical server via ZoneEdit. The longer the server is around and the more projects I work on the more I have realized I need that local mail to be delivered to my normal email for debugging of applications, logwatch, etc...

I was trying to use Postfix following several similar users' issues online. (Relaying local mail to Gmail/Google Apps using Postfix). Some of the tutorials I have tested are; The Prancing Tarantula (http://prantran.blogspot.com/2007/01/getting-postfix-to-work-on-ubuntu-with.html ), Setting up Postfix to relay through Gmail (http://www.darryl.cain.com.au/postfix/ ), and How to relay mail using Ubuntu, Postfix, and Gmail (http://kirranet.co.nz/content/howto-relay-email-using-ubuntu,-postfix-and-gmail ). None have worked.

I can get Postfix to say the message was sent, yet it never leaves the local mailbox, and it is nowhere to be found. From the tutorials I have learned there is an issue with Google and TLS so a certificate needs to be created. A simple relay will not work. So my problem still stands, i cannot get local mail relayed/forwarded. Does anyone have any ideas how I can relay local mail delivered to, say root, to my Google Apps account? Anyone?

Server Info: Ubuntu 7.10 Server


---
Chad R Mayfield
[EMAIL PROTECTED]
GPG Key: 0C9A026F
http://www.planetmayfield.com/
http://www.chadmayfield.com/






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